The mysterious figure of Holy Sophia - the Wisdom of God - is a common motive of the medieval East European sacral art and a considerable part of modern Russian religious philosophy. Many representatives of the latter developed the so called sophiology, i.e., a mystical, but at the same time speculative, synthesis based on intuition of organic unity of the whole Universe in the creative intention of God. Within the limits of this poetical metaphysics, they tried to express a concrete all-embracing idea, a collective archetype of all things, using a biblical personification of Wisdom - female companion of the Creator described in the Book of Proverbs (Chapter 8). Likewise, old Russian icons, especially those of Novgorod tradition, present a symbolical figure of Holy Wisdom (Sophia) as an Angel sitting on a throne, Christ over his head, and Mother of God and John the Baptist standing beside. Here, the symbolical figure of Sophia expresses the sphere of contact between the Creator and the creature - their mystical meeting point in wisdom which is identical with chastity. The paper is a short outline of various theological interpretations of the figure of Sophia in ecclesial tradition (her 'hypostatic' identifications as Christ-Logos, Virgin Mary or Ecclesia). It includes interpretations of Holy Sophia icons in the thought of Russian philosophers: Evgeniy Trubetskoy, Pavel Florensky and Sergey Averintsev, and discussion of the current value of symbolical theology, included both in the outlook on life of medieval Orthodox painters and in Russian philosophical reflection from the turn of the 20th century.
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